This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Repinotan
Accession Number
DB06506
Type
Small Molecule
Groups
Investigational
Description

Repinotan is a high-affinity, selective, full agonist of the 5HT1A-receptor subtype with neuroprotective properties.

Structure
Thumb
Synonyms
  • Repinotan
Product Ingredients
IngredientUNIICASInChI Key
Repinotan hydrochloride1KBQ63168A144980-77-8IGKYREHZJIHPML-UNTBIKODSA-N
Categories
UNII
05PB82Z52L
CAS number
144980-29-0
Weight
Average: 400.49
Monoisotopic: 400.145678435
Chemical Formula
C21H24N2O4S
InChI Key
YGYBFMRFXNDIPO-QGZVFWFLSA-N
InChI
InChI=1S/C21H24N2O4S/c24-21-18-8-2-4-10-20(18)28(25,26)23(21)14-6-5-13-22-15-17-12-11-16-7-1-3-9-19(16)27-17/h1-4,7-10,17,22H,5-6,11-15H2/t17-/m1/s1
IUPAC Name
2-[4-({[(2R)-3,4-dihydro-2H-1-benzopyran-2-yl]methyl}amino)butyl]-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione
SMILES
O=C1N(CCCCNC[C@H]2CCC3=CC=CC=C3O2)S(=O)(=O)C2=CC=CC=C12

Pharmacology

Indication

Investigated for use/treatment in strokes, cerebral ischemia, and depression.

Pharmacodynamics
Not Available
Mechanism of action

Repinotan is a 5-HT1A receptor agonist which inhibits glutamate induced depolarization. The effect of repinotan in neuronal cells has been reported to be mediated by a variety of mechanisms/signaling pathways, including activation of the anti-apoptotic phosphatidylinositol 3-kinase (PI-3K) pathway, inhibition of glutamate release (probably via opening of K+ channels leading to membrane hyperpolarization), extracellular-regulated kinase (Erk)-stimulated Bcl-2 expression or inhibition of caspase-3 activity, and increased release of the neurite extension factor S-100 beta.

TargetActionsOrganism
U5-hydroxytryptamine receptor 1ANot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Repinotan is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Repinotan is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Repinotan is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Repinotan.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Repinotan is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Repinotan.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Repinotan is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Repinotan.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Repinotan is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbataceptThe metabolism of Repinotan can be increased when combined with Abatacept.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
172029
ChEMBL
CHEMBL1614652
Wikipedia
Repinotan

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAcute Ischemic Stroke (AIS) / Strokes1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0059 mg/mLALOGPS
logP2.11ALOGPS
logP3.07ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)9.63ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area75.71 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.66 m3·mol-1ChemAxon
Polarizability42.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
1-benzopyrans
Alternative Parents
Benzothiazoles / Aralkylamines / Alkyl aryl ethers / Benzenoids / Organosulfonic acids and derivatives / Amino acids and derivatives / Oxacyclic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
1-benzopyran / 1,2-benzothiazole / Alkyl aryl ether / Aralkylamine / Benzenoid / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Amino acid or derivatives / Carboxylic acid derivative / Secondary aliphatic amine
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Tanigawa T, Heinig R, Kuroki Y, Higuchi S: Evaluation of interethnic differences in repinotan pharmacokinetics by using population approach. Drug Metab Pharmacokinet. 2006 Feb;21(1):61-9. [PubMed:16547395]

Drug created on March 19, 2008 10:35 / Updated on June 04, 2019 06:24